Water → 2-(1-Methyl-4-piperidyl)-1-(2-phenyl-4-quinolyl)-ethanol

HRID 65220Notes

Reaction equation

HRID 65220 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([CH:17]([OH:25])[CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[C:28](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:28][N:22]1[CH2:23][CH2:24][CH:19]([CH2:18][CH:17]([C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:16]=2)[OH:25])[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 130752861-(2-Phenyl-4-quinolyl)-2-(4-piperidyl)-ethanol

Product 1

HCID 155816742-(1-Methyl-4-piperidyl)-1-(2-phenyl-4-quinolyl)-ethanolYield 37.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.55 g of 1-(2-phenyl-4-quinolyl)-2-(4-piperidyl)-ethanol (racemic), 1.1 g of methyl iodide and 0.6 g of potassium carbonate in 20 ml of dimethylformamide was stirred for 2 hours at the ambient temperature. 20 ml of water and 30 ml of toluene were then added. The organic phase was separated, wahsed with water, dried over magnesium sulfate and evaporated under reduced pressure. 1 g of crude product was obtained which was fixed on a column of silica gel. The elution was effected with a 9/1 chloroform-diethylamine mixture. 0.57 g of 2-(1-methyl-4-piperidyl)-1-(2-phenyl-4-quinolyl)-ethanol (racemic), which melted at 208° C. was thus isolated.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. custom1 g of crude product was obtained which
  5. washThe elution

Sources & evidence

ORD record
ord-3e1c7d050ac640d99fdcd095c742432d
Source dataset
uspto-grants-1986_09
Patent number
US04613607

Reaction notes

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